None ever are for the manager of Newcastle United, certainly not during the Mike Ashley era at least, but this has been a particularly complex one for Benitez to attempt to navigate.

A lack of funds, the need to augment his budget by selling some of his fringe players, an inflated wage bill which needs reducing, an owner attempting to sell and unwilling to put additional finances into the club, as well as the ongoing uncertainty over his own long-term future and the ambition which Newcastle’s hierarchy holds, have all contributed to making this arguably one of the most-challenging transfer windows in Benitez’s illustrious career.

Such a complex set of circumstances has led Benitez to take what one insider at St James’ Park has described as an “open-minded approach” to the business he must undertake.

That is why Newcastle are contemplating the sale of players who fans would never have envisaged Benitez offloading this summer; the United manager would ideally like to keep the first-team players who have served him so well up until now in order to increase competition, but wheeling and dealing is something which the Spaniard has recognised may become a necessity.

Matt Ritchie of Newcastle United (Image: Getty Images Europe)

Why would Benitez contemplate selling Matt Ritchie?

Take Matt Ritchie for example. The Scotland international is one of Benitez’s most-trusted lieutenants, and the 28-year-old is someone Benitez signed during the summer of 2016 with the Premier League in mind; Ritchie had an excellent record in the Championship, but he also had the attributes to excel in the top flight, too.

Remember, when Newcastle initially baulked at AFC Bournemouth’s £12million asking price for Ritchie - deeming the winger to be worth £10m - it was Benitez who personally intervened to convince the hierarchy to sanction the deal, promising them the wideman would come good on the investment.

His 15 goals and 12 assists across two campaigns, as well as his key contributions in aiding Newcastle clinch promotion from the Championship and then a 10th-placed Premier League finish last term, prove that he already has.

There is also little doubt that Ritchie, who has three years remaining on his United deal, still has a lot more to give Newcastle, too.

Video Loading

Video Unavailable

Click to playTap to play

The video will start in 8Cancel

Play now

He is a senior voice in the dressing room, he has an infectious work ethic and will to win which rubs off on other Magpies - when Ritchie plays well, United tend to play well - while off the pitch he has already established deep roots in the area, including setting up the Newcastle Elite Academy with three of his team-mates.

However, although Ritchie played a key role in Newcastle’s success last season, he is not quite as effective in the Premier League as he is in the Championship.

A lack of pace is Ritchie’s biggest weakness and, though he whips in crosses from deep and can take an excellent set piece, the most-dangerous wingers in the Premier League have devastating speed.

This is not to criticise Ritchie; he is a very good operator for Newcastle, and can still play a key role for the club going forward.

Ideally Benitez would like to keep Ritchie and then bring in other widemen to create increased competition, as well hand the United manager alternative options.

Newcastle United manager Rafa Benitez (Image: Getty Images Europe)

The need for pace and a ‘X factor’

But Benitez also knows United must avoid ‘second-season syndrome’. The Magpies confounded expectations to secure a 10th-placed finish last term, but there will be no surprise element to their play in 2018/19 unless some alterations are made and new players signed.

Newcastle must evolve - and, in order to do so, they need to add raw pace and a ‘X factor’ to their attacking arsenal.

That is exactly what Kenedy did once he arrived in January, and the 22-year-old Brazilian still has plenty of room to improve.

It was no coincidence that Newcastle’s excellent run between February and April coincided with the versatile wideman being added to the starting line up.

He may have only scored twice and provided two assists, but his impact was far more significant than that; his set-piece delivery, his speed on the break and his self-belief were extremely important, too.

Benitez himself was most impressed by Kenedy’s desire to receive possession and attempt to play from anywhere; that confidence ensured the winger would get the ball and look to hurt the opposition whenever he could.

Ensuring these elements are present in the side again next season is essential to Newcastle’s hopes of improving and establishing themselves as a top-10 side as Benitez desires.

But the £30m fee Chelsea are currently quoting United would represent a significant portion of Benitez’s summer budget.

If Aleksandar Mitrovic can be sold for the best part of £20m, then Benitez will have some additional money to spend - yet, with a frontline striker still needed too, those funds will not stretch far enough.

That is why Ritchie could be sold if an enticing offer north of £15m is lodged by one of AFC Bournemouth, Middlesbrough or, most likely, Stoke City.

Newcastle United's Kenedy celebrates scoring his side's first goal of the game during the Premier League match at St James' Park (Image: PA)

Speed down both flanks would make Newcastle more effective against the top six

If United did sign Kenedy then, realistically, the Magpies would find themselves in a similar position to where they were come the end of last season.

Benitez wants to add a fresh dimension to his side, and one way in which he seems to believe he can do so is by bringing in additional pace on both flanks.

That’s where Andros Townsend comes in. He is someone Benitez never wanted to leave in the first place - the Spaniard tried to convince Townsend to stay three times once Crystal Palace activated the £13m release clause in his deal two years ago - and United have been keen on a reunion with the winger ever since.

Read More

His speed, willingness to take on full-backs, and ability to cross with both feet make the 26-year-old a versatile option.

If Benitez could send out a team with Kenedy on one flank and Townsend on the other - and give them the freedom to interchange at will - then Newcastle would have the sort of pace and unpredictable attacking weapons out wide that will cause all top-flight teams problems.

Away at top-six sides last season, Newcastle essentially played to protect their goal difference, but with Kenedy and Townsend they would have real counter-attacking weapons who would give United real hope of securing positive results at such grounds.

They would also be extremely effective at St James’ Park, too. If sides come to Tyneside and defend, then Newcastle would have a real threat on both flanks - which would increase the chances of United being able to break down the opposition.

Andros Townsend of Crystal Palace (Image: Getty Images Europe)

If an ‘upgrade’ is possible, Benitez is willing to wheel and deal

Ideally, Benitez would hope to keep Ritchie as well as sign Townsend and Kenedy; then Newcastle would have serious strength in depth out wide.

But the limited budget Benitez has at his disposal means he must consider any substantial bid which is received for one of his current first-team players, and then judge whether he can use those funds to ‘upgrade’ areas of his team.

Read More

If a deal for Kenedy or Townsend can be part-financed by the sale of Ritchie, then it is something Benitez will examine.

There is no room for sentiment as far as Benitez is concerned - even if he would rather not be forced into a position where he feels he must sell as a first-team player in order to finance the arrival of an ‘upgrade’.